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Issue 34, 2011
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Synthesis and antioxidant capacity of 5-selenopyranose derivatives

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Abstract

Described is a convenient method for the syntheses of sulfur and selenium containing carbohydrate derivatives of L-gulodeoxynojirimycin and the corresponding C-5 epimer D-mannodeoxynojirimycin. The key step in the synthesis of the latter involves epimerisation of the C-5 hydroxyl group by an oxidation followed by stereo-selective reduction to obtain the desired D-sugar derivative. Both derivatives displayed a dose-dependent prevention of the oxidation of methionine residues on human plasma proteins induced by the inflammatory oxidant hypochlorous acid. The seleno-analogues were considerably more active than their thio-equivalents.

Graphical abstract: Synthesis and antioxidant capacity of 5-selenopyranose derivatives

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Publication details

The article was received on 20 Jun 2011, accepted on 15 Jul 2011 and first published on 29 Jul 2011


Article type: Communication
DOI: 10.1039/C1CC13652F
Chem. Commun., 2011,47, 9693-9695

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    Synthesis and antioxidant capacity of 5-selenopyranose derivatives

    C. Storkey, M. J. Davies, J. M. White and C. H. Schiesser, Chem. Commun., 2011, 47, 9693
    DOI: 10.1039/C1CC13652F

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